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Ambipolar host in organic light emitting diode

a light-emitting diode and ambipolar host technology, applied in the direction of discharge tube luminescnet screen, other domestic articles, natural mineral layered products, etc., can solve the problems of unbalanced hole-transport and electron-transport properties, aggregation and lack of uniformity, and uneven material degradation ra

Active Publication Date: 2011-08-23
SAMSUNG ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The proposed host materials achieve high quantum efficiency, low turn-on voltage, and balanced charge transport, leading to improved device performance and cost-effectiveness in WOLEDs by reducing the need for expensive emissive materials and simplifying device fabrication.

Problems solved by technology

Most currently used host materials are a mixture of hole-transport material and electron-transport material, which may pose potential problems of phase separation, aggregation and lack of uniformity, and unequal material degradation rates.
However, these molecules have either unbalanced hole-transport and electron-transport properties, or the devices made from these molecules have only moderate efficiency.

Method used

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  • Ambipolar host in organic light emitting diode
  • Ambipolar host in organic light emitting diode
  • Ambipolar host in organic light emitting diode

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0100]An example of the host compound may be synthesized according to the following scheme:

[0101]

Experimental

[0102]Bromo-Py-Cbz (1). Compound 1 was made according to a procedure adapted from Hou, Z.; Liu, Y.; Nishiura, M.; Wang, Y. J. Am. Chem. Soc. 2006, 128(17), 5592-5593. A mixture of carbazole (4.751 g, 28.41 mmol), 3,5-dibromopyridine (20.19 g, 85.23 mmol), K2CO3 (15.71 g, 113.6 mmol), copper powder (1.204 g, 18.94 mmol), 18-crown-6 ether (2.503 g, 9.470 mmol) and 1,2-dichlorobenzene (150 mL) was degassed with argon for 1 h while stirring. The reaction mixture was then maintained at 200° C. with stirring under argon for 20 h. Upon cooling to RT, the crude mixture was filtered and concentrated in vacuo. The resulting residue was then purified by flash chromatography (SiO2, 1:1 to 11:9 dichloromethane-hexanes) to afford 1 (6.75 g, 74%) as a white solid: mp=118-120° C.; 1H NMR (400 MHz, CDCl3): δ 8.81 (dd, J=23.2, 2.0 Hz, 2H), 8.14 (d, J=7.7 Hz, 2H), 8.10 (t, J=2.2 Hz, 1H), 7.47-7...

example 2

[0105]Fabrication of Device C: ITO coated glass substrates were cleaned by ultrasound in acetone and 2-propanol, consecutively, then baked at 110° C. for 3 hours, followed by treatment with oxygen plasma for 5 min. A layer of PEDOT: PSS (Baytron P from H. C. Starck) was spin-coated at 3000 rpm onto the pre-cleaned and O2-plasma treated (ITO)-substrate and annealed at 180° C. for 10 min, yielding a thickness of around 40 nm. In a glove-box hosted vacuum deposition system at a pressure of 10−7 torr (1 torr=133.322 Pa), 4,4′4″-tri(N-carbazolyl)triphenylamine (TCTA) was first deposited on top of PEDOT / PSS layer at deposition rate of 0.06 nm / s, yielding a 30 nm thick film. Then Dicbz-Bipy and platinum(II)(2-(4′,6′-difluorophenyl)pyridinato-N,C2′)(2,4-pentanedionato) (FPt) were concurrently heated and deposited on top of TCTA under different deposition speed to make FPt at 12 wt %, followed by deposition of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) at deposition rate around 0.06...

example 3

[0106]The ambipolar property of Dicbz-Bipy was evaluated using Devices A and B. Device A was fabricated as following: ITO-coated glass substrates were cleaned by ultrasound in acetone and 2-propanol, consecutively, then baked at 110° C. for 3 hours, followed by treatment with oxygen plasma for 5 min. A layer of PEDOT: PSS (Baytron P from H. C. Starck) was spin-coated at 3000 rpm onto the pre-cleaned and O2-plasma treated (ITO)-substrate and annealed at 180° C. for 10 min, yielding a thickness of around 40 nm. In a glove-box hosted vacuum deposition system at a pressure of 10−7 torr (1 torr=133.322 Pa) was Dicbz-Bipy first deposited on top of PEDOT / PSS layer at deposition rate of 0.06 nm / s, followed by deposition of Al at deposition rates of 0.2 nm / s.

[0107]Device B was fabricated as following: ITO-coated glass substrates were cleaned by ultrasound in acetone and 2-propanol, consecutively, then baked at 110° C. for 3 hours, followed by treatment with oxygen plasma for 5 min. In a glov...

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Abstract

Some embodiments provide a compound represented by Formula 1:wherein R1, R2, R3, R6, R7, and R8 are independently selected from the group consisting of H, optionally substituted C1-12 alkyl, optionally substituted phenyl, optionally substituted carbazolyl, optionally substituted diphenylamine and optionally substituted diphenylaminophenyl; provided that: at least one of R1, R2, and R3 is selected from optionally substituted carbazolyl, optionally substituted diphenylamine and optionally substituted diphenylaminophenyl and at least one of R6, R7, and R8 is selected from optionally substituted carbazolyl, optionally substituted diphenylamine and optionally substituted diphenylaminophenyl; and R4 and R5 are independently selected from the group consisting of H, optionally substituted C1-12 alkyl, optionally substituted phenyl, optionally substituted diphenylamine and optionally substituted diphenylaminophenyl. Other embodiments provide an organic light-emitting diode device comprising a compound of Formula I.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Application No. 61 / 149,560, filed Feb. 3, 2009, which is incorporated by reference herein in its entirety.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]This invention relates to compounds for use in organic light emitting diodes, such as for host materials.[0004]2. Description of the Related Art[0005]White organic light emitting devices (WOLEDs) have attracted much attention and been intensively studied due to their potential applications as backlight sources, full color displays, and general lighting. Among various device configurations to produce white light, a single-emissive-layer device employing phosphorescent materials in combination with proper host materials is desirable. Some advantages of such device may include reduced overall cost, increased quantum efficiency and easier fabrication. Since phosphorescent emitters can harvest both singlet and triplet exc...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01L51/54C07D401/14H10K99/00
CPCC07D213/38C07D401/14C09K11/06H01L51/0072H05B33/20H01L51/0067C09K2211/1022C09K2211/1029H01L51/0037Y10S428/917H01L51/0085H01L51/5016H01L51/5036H10K85/1135H10K85/654H10K85/6572H10K85/342H10K50/125H10K50/11H10K2101/10
Inventor SISK, DAVID T.LI, SHENGMOCHIZUKI, AMANE
Owner SAMSUNG ELECTRONICS CO LTD